Wow. It was awesome.

16 people flew from 9 US states plus India, China, and Spain to meet in Orlando for 8 days. We’ve been in business for four years. To date, we’ve never all met in-person. Some of us have never met outside of video chat. We’ve also doubled our team size in the last six months and introduced middle management. This article is about what worked and didn’t work.


  • Everyone in one house. We got an 11 bedroom with extra cots. It was awesome waking up with everyone in the same kitchen and pool area, learning about everyone’s eating and living styles, and learning more about how the team operates. This has already led to a more aligned understanding of the interactions of our team. I’m not surprised, but am pleased that there were no negative things that occurred between teammates (that I’m aware of at least).
  • A set agenda (see below). We planned months out. High level: Saturday through Monday, show up whenever you want. Tuesday, Hackathon. Wednesday, Predictive Index training. Thursday, I spoke to the team on our future, financials, option grants, and my gratitude for who I get to work with, a team member spoke on the meaning of option grants for personal financial benefit, and another spoke on our product process. Friday was on scorecards, our mission statement, and most importantly, an exercise called Feedback Circles, where we broke out into small groups and one by one, told one teammate what they do well and what they need to work on, each taking turns, followed by volunteering. Saturday was Universal Studios then a nice sushi dinner. Sunday we headed out.
  • A pool. The team loved sitting around it, swimming, tossing me in (multiple times, clothes and wallet, no phone), floating on alligator and orca pool blowups, and soaking up the pool’s energy. There was a calm about it.


  • Team casual meals and gatherings in the kitchen. Having a big central meeting space. There’s something about the classic “breaking bread with friends” concept that truly works. Our Indian teammates were teaching us the proper way to move your head side to side with a yes or no, our Spanish-speaking teammates on fun words, and our American teammates having our international teammates try American foods. The mixing of cultures in the kitchen was simply awesome.
  • A living room with lots of seating. Biz broke out constantly, everywhere: How to manage a sales process, market an app, structure our platform to scale, tools we should be leveraging, the best way to manage a growing team, etc…
…Read more (about what didn’t work and see more photos from the trip) here.